EP0175840A3 - Racemisation process of n-acetyl-d(l)-alpha-amino-carboxylic-acids - Google Patents

Racemisation process of n-acetyl-d(l)-alpha-amino-carboxylic-acids Download PDF

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Publication number
EP0175840A3
EP0175840A3 EP85106048A EP85106048A EP0175840A3 EP 0175840 A3 EP0175840 A3 EP 0175840A3 EP 85106048 A EP85106048 A EP 85106048A EP 85106048 A EP85106048 A EP 85106048A EP 0175840 A3 EP0175840 A3 EP 0175840A3
Authority
EP
European Patent Office
Prior art keywords
acetyl
alpha
melt
acids
temperature
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP85106048A
Other languages
German (de)
Other versions
EP0175840B1 (en
EP0175840A2 (en
Inventor
Michael Dr. Karrenbauer
Axel Dr. Kleemann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Degussa GmbH filed Critical Degussa GmbH
Priority to AT85106048T priority Critical patent/ATE37705T1/en
Publication of EP0175840A2 publication Critical patent/EP0175840A2/en
Publication of EP0175840A3 publication Critical patent/EP0175840A3/en
Application granted granted Critical
Publication of EP0175840B1 publication Critical patent/EP0175840B1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

N-acetyl-D(L)- alpha -aminocarboxylic acids are thermally racemized by melting, adding a small amount of acetic anhydride to the melt and heating to a temperature between the melting temperature and about 210 DEG C. and subsequently quenching the melt with an aqueous alkali metal hydroxide or ammonia solution. The residence time needed for complete racemization depends on the heating temperature of the melt in the manner that the higher the heating temperature the shorter the residence time.
EP85106048A 1984-09-25 1985-05-17 Racemisation process of n-acetyl-d(l)-alpha-amino-carboxylic-acids Expired EP0175840B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85106048T ATE37705T1 (en) 1984-09-25 1985-05-17 PROCEDURE FOR THE RACEMIZATION OF N-ACETYL-D(L)ALPHA-AMINOCARBONIC ACIDS.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3435095 1984-09-25
DE3435095A DE3435095C2 (en) 1984-09-25 1984-09-25 Process for the racemization of N-acetyl-D (L) -α-amino carboxylic acids

Publications (3)

Publication Number Publication Date
EP0175840A2 EP0175840A2 (en) 1986-04-02
EP0175840A3 true EP0175840A3 (en) 1987-03-25
EP0175840B1 EP0175840B1 (en) 1988-10-05

Family

ID=6246268

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85106048A Expired EP0175840B1 (en) 1984-09-25 1985-05-17 Racemisation process of n-acetyl-d(l)-alpha-amino-carboxylic-acids

Country Status (8)

Country Link
US (1) US4602096A (en)
EP (1) EP0175840B1 (en)
JP (1) JPS6185351A (en)
AT (1) ATE37705T1 (en)
CA (1) CA1249994A (en)
DE (2) DE3435095C2 (en)
HU (1) HU197561B (en)
IL (1) IL75588A (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4981799A (en) * 1987-08-21 1991-01-01 Takeda Chemical Industries, Ltd. Acylamino acid racemase, production and use thereof
DE3817191A1 (en) * 1988-05-20 1989-11-30 Hoechst Ag METHOD FOR RACEMIZING OPTICALLY ACTIVE D-2-N-PHENACETYLAMINO-4-METHYLPHOSPHINOBUTTERIC ACID
US4946997A (en) * 1989-06-07 1990-08-07 Merck & Co., Inc. Racemization of a carboxylic acid
AU695740B2 (en) * 1994-10-07 1998-08-20 Darwin Discovery Limited Racemisation of precursors to levobupivacaine and analogues thereof
US6156900A (en) * 1994-10-07 2000-12-05 Darwin Discovery Limited Racemization of precursors to levobupivacaine and analogues thereof
DE19546532C2 (en) * 1995-12-13 2000-04-20 Degussa Process for obtaining optically active L-alpha-aminocarboxylic acids from corresponding racemic D, L-alpha-aminocarboxylic acids
DE19546531A1 (en) * 1995-12-13 1997-06-19 Degussa Process for the racemization of N-acetyl-D (L) -alpha-aminocarboxylic acids
US6114163A (en) * 1995-12-13 2000-09-05 Degussa Aktiengesellschaft Process for obtaining active L-α-amino carboxylic acids from corresponding racemic d, L-α-amino carboxylic acids
US6080887A (en) * 1996-12-05 2000-06-27 Degussa Aktiengesellschaft Process for racemization of N-acetyl-(D)L-α-amino carboxylic acids
DE10013599A1 (en) * 2000-03-18 2001-09-20 Aventis Res & Tech Gmbh & Co Process for the racemization of N-acylamino acids using transition metal catalysts

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1964420A1 (en) * 1968-12-27 1970-07-16 Hoffmann La Roche Resolution
FR2074022A5 (en) * 1969-12-20 1971-10-01 Dynamit Nobel Ag
EP0137371A2 (en) * 1983-09-27 1985-04-17 Hoechst Aktiengesellschaft Process for the racemisation of optically active aminoacids

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2071327A (en) * 1935-08-15 1937-02-23 Rudolph S Bley Process of racemizing amino acids
US3213106A (en) * 1961-11-16 1965-10-19 Ajinomoto Kk Process of racemizing optically active alpha acids
US3458568A (en) * 1965-02-19 1969-07-29 Toa Gosei Chem Ind Process for preparing an optically inactive amino acid from an optically active amino acid
US3737454A (en) * 1969-09-10 1973-06-05 Tanabe Seiyaku Co Racemization of optically active ammonium n-acetyl-alpha-aminophenylacetate
JPS5318006B2 (en) * 1973-09-28 1978-06-13

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1964420A1 (en) * 1968-12-27 1970-07-16 Hoffmann La Roche Resolution
FR2074022A5 (en) * 1969-12-20 1971-10-01 Dynamit Nobel Ag
EP0137371A2 (en) * 1983-09-27 1985-04-17 Hoechst Aktiengesellschaft Process for the racemisation of optically active aminoacids

Also Published As

Publication number Publication date
DE3435095A1 (en) 1986-03-27
HUT41381A (en) 1987-04-28
EP0175840B1 (en) 1988-10-05
CA1249994A (en) 1989-02-14
US4602096A (en) 1986-07-22
HU197561B (en) 1989-04-28
JPS6185351A (en) 1986-04-30
DE3435095C2 (en) 1986-07-24
EP0175840A2 (en) 1986-04-02
DE3565393D1 (en) 1988-11-10
IL75588A (en) 1988-08-31
IL75588A0 (en) 1985-10-31
JPH0339491B2 (en) 1991-06-14
ATE37705T1 (en) 1988-10-15

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